Pyridine → HCID 178491768, compound

HRID 1271531Notes

Reaction equation

HRID 1271531 reaction equation
[NH:1]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:2]([C:24]([OH:26])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:23])[NH:8][S:9]([C:12]1[C:21]([CH3:22])=[C:19]([CH3:20])[C:16]([O:17][CH3:18])=[CH:15][C:13]=1[CH3:14])(=[O:11])=[O:10].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1F>C(Cl)Cl>[C:30]([O:29][C:27](=[O:28])[NH:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]([C:7](=[NH:23])[NH:8][S:9]([C:12]2[C:13]([CH3:14])=[CH:15][C:16]([O:17][CH3:18])=[C:19]([CH3:20])[C:21]=2[CH3:22])(=[O:11])=[O:10])[C:24]1=[O:26])([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 178491780HCID 178491780, compound

Product 1

HCID 178491768HCID 178491768, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of Boc-Arg(Mtr)-OH (6.81 g, 14 mmol) and pyridine (1.11 g, 14 mmol) in CH2Cl2 (50 mL) at −20° C. was added cyanuric fluoride (9.45 g, 70 mmol). After addition, the reaction mixture was stirred at −10° C. for 1.5 hours. The reaction mixture was quenched with an ice-H2O mixture and CH2Cl2 (50 mL), the resulting suspension was filtered through a pad of Celite and the two clear layers were separated. The aqueous layer was extracted with CH2Cl2 (50 mL)). The combined organic layer was washed with H2O (50 mL), and dried over MgSO4. After filtration and concentration, the crude oil was dissolved in CH2Cl2 and triturated in hexane. The title product was obtained as a white solid by vacuum filtration.

Workup

  1. additionAfter addition
  2. customThe reaction mixture was quenched with an ice-H2O mixture and CH2Cl2 (50 mL)
  3. filtrationthe resulting suspension was filtered through a pad of Celite
  4. customthe two clear layers were separated
  5. extractionThe aqueous layer was extracted with CH2Cl2 (50 mL))
  6. washThe combined organic layer was washed with H2O (50 mL)
  7. dry with materialdried over MgSO4
  8. filtrationAfter filtration and concentration
  9. dissolutionthe crude oil was dissolved in CH2Cl2
  10. customtriturated in hexane

Sources & evidence

ORD record
ord-4dfa1a2224dd45548079c9cc4f451055
Source dataset
uspto-grants-2007_04
Patent number
US07205384B2

Reaction notes

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